2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Details

• Internal ID: 3bf45c3d-b5aa-469e-81f4-06c0f80ed10a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@@H](C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21?/m1/s1
• InChI Key: OXGUCUVFOIWWQJ-GPTQEAJUSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.49
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• SCHEMBL117644
• CHEMBL479232
• AKOS030242369
• 3',4',5,7-Tetrahydroxy-3alpha-(D-rhamnopyranosyloxy)flavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8357	83.57%
Caco-2	-	0.7858	78.58%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7163	71.63%
OATP2B1 inhibitior	+	0.5902	59.02%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9188	91.88%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6264	62.64%
P-glycoprotein inhibitior	-	0.5351	53.51%
P-glycoprotein substrate	-	0.6786	67.86%
CYP3A4 substrate	+	0.6264	62.64%
CYP2C9 substrate	-	0.7038	70.38%
CYP2D6 substrate	-	0.8611	86.11%
CYP3A4 inhibition	-	0.7109	71.09%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8339	83.39%
CYP2D6 inhibition	-	0.9547	95.47%
CYP1A2 inhibition	-	0.5306	53.06%
CYP2C8 inhibition	+	0.9061	90.61%
CYP inhibitory promiscuity	-	0.5648	56.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6170	61.70%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.7424	74.24%
Skin irritation	-	0.6220	62.20%
Skin corrosion	-	0.9360	93.60%
Ames mutagenesis	+	0.5863	58.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6352	63.52%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8874	88.74%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8191	81.91%
Acute Oral Toxicity (c)	III	0.5184	51.84%
Estrogen receptor binding	+	0.6589	65.89%
Androgen receptor binding	+	0.7443	74.43%
Thyroid receptor binding	+	0.5667	56.67%
Glucocorticoid receptor binding	+	0.7217	72.17%
Aromatase binding	-	0.5140	51.40%
PPAR gamma	+	0.6941	69.41%
Honey bee toxicity	-	0.7943	79.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5050	50.50%
Fish aquatic toxicity	+	0.9457	94.57%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1900	P15121	Aldose reductase	150 nM	IC50	via Super-PRED
CHEMBL3729	P22748	Carbonic anhydrase IV	67.3 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	3.9 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	43.5 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.27%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.14%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.95%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.47%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.04%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.01%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.54%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	90.50%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.82%	95.56%
CHEMBL3194	P02766	Transthyretin	87.42%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.11%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.55%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.06%	96.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	84.30%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.11%	99.23%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.02%	93.65%
CHEMBL4208	P20618	Proteasome component C5	82.43%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.26%	80.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.95%	97.36%

Plants that contains it

• Bupleurum chinense
• Epimedium sagittatum
• Harpephyllum caffrum
• Houttuynia cordata
• Rosa chinensis

Cross-Links

• PubChem: 18604930
• NPASS: NPC317489
• ChEMBL: CHEMBL479232
• LOTUS: LTS0061465
• wikiData: Q105202607